Silver compound of the acridin series and a process of making same.



UNITED STATES PATENT oFFIcE.

PAUL HIISSY AND MAX HARTMANN, OF DASEL, SWITZERLAND, ASSIGNOBS T0 SCCIETY OF CHEMICAL INDUSTRY IN BASLE, OF BASEL, SWITZERLAND.

SILVER COMPOUND OF 'II-IE ACRIDIN SERIES AN D'A PROCESS OF MAKING SAME.

No Drawing.

To all 'w/wm z'tmay/cuncem:

lie it known that we, Dr. Med. lAUL l-Iii'ssY aml Dr. Phil. l\l.\X lla-irrwmxn, both citizens of the Swiss Republic, and residents of Basel, Switzerland, have invented new and useful Silver Compounds of the Acridin Series and a Process of lllaking Same, of which the following is a full, clear, and exact specification.

\Ve have found, that valuable disinfectants of the acridin series are obtained, by acting with a. soluble silver salt, on acridin dyestuffs, which may be 'alkylated at the acridin nitrogen, in presence of a convenient solvent, as for instance water or alcohol. The thus obtained well. defined crystalline compounds possess a prominent bactericidc action much' superior to that of the heretofore known disinfectants with dyestuli" character, as for instance the acridin dyestuffs employed as parent niaterial or certain derivatives of other basic dyestuffs, as for instance of the methylene. blue. or rhodamin series. Thus, for instance, the silver salts of the acridi-n derivatives alkylat-ed at the acridin. nitrogen act even in a state of the greatest dilution (1:150000 to 14180000) still growth checking, especially on strep tococcus and splenitis bacilli, while the said alkylatcd acridin derivatives themselves show only a feeble development checking action already in dilution of 17.80000.

The toxicity of the new silver compounds is generally a. trifling. one and within the limits allowed for injection purposes, wherefore the new compounds are appli- -able for injections. 1

For the preparation of the. new com pounds can be added. for instance, to a solution as concentrated as possible of the desired acridin d vestutl salt in a. convenient solvent, as for instance, water or alcohol, a. likewise. concentrated solution of a silver salt soluble in the employed solvent, whereupon the. crystallization of the silver com pound formed begins mostly after a. short time and can be completed by refrigerating or, if desired, by adding a convenient precipitating agent, as for instance, ether. The

separation of the new compounds is effected in the usual manner by filtration, washing and drying. r

The new disinfectants constitute red to black powders, which dissolve in water with red to green coloration, in alcohol, acetic Specification of Letters Patent.

Application filed January 23, 1917.

Patented May 29, 1917.

Serial No. 144,081.

ether, glacial acetic acid and-acetone with a strong fluorescence and in concentrated sulfuric acid with yellow to red colorations.

The process is illustrated by the following examples Example 1: 12.5 parts of the chemically pure nitrate of the acridin dyestutl methylated at the acridin nitrogen, obtained in the known manner by heating 2 :7-dimethyl-3 :6- diaminoacridin with methyl chlorid under pressure, are dissolved in as small a quantity as possible of boiling distilled water and hereafter a solution of 7.8 parts silver nitrate in a small quantity of water is added to the solution. The'new silver compound separates immediately in the form of a crystalline tilered precipitate; the. separation is completed by cooling the mass or by allowing the same to stand for a certain time. llereafter the precipitate is filtered water and afterward with alcohol and ether and dried in wmzm. The new silver compound constitutes in a drystate a brownred powder, dissolving in water to redorange solutions, in alcohol with orange-yet low coloration and strong fluorescence, in acetone, acetic ether and glacial acetic acid with yellow-green fluorescence and in concentrated sulfuric acid with yellow pure coloration; it is insoluble in ether.

Example 2: 20 parts 326-diamidoacridin in form of the pure base are suspended into a small quantity of hot water and to the thus obtained suspension is added, while stirring, pure nitr': acid, until the dyestuit is completely dissolved. Then a solution of 17 parts silver nitrate in 50,-parts water is :ulded, whereby the black-brown silver compound separates. After the mass has been allowd to stand for a certain time, the new silver compound is isolated by filtration, washed and dried in 'lamm. It. constitutes a blue powder, which dissolves in water with green colorations and in alcohol, acetone and acetic ether with yellow-green fluorescence and in glacial acetic acid with a brown-red coloration. It dissolves in concentrated sulfuric acid to Wine-red coloration of strong fluorescence; it is insoluble in'ether.

Example 3: 2.6 parts diaminomethylacridinium nitrate are dissolved in a small quantity of alcohol and to the obtained solution is added a solution of 2.8 parts sllvcr BEST AVAlLABLE cop phenolsulfonate in hot alcohol. The mass is hereafter diluted with an equal volume of ether and the silver compound separated in the fullli of flakes is isolated by filtration. After drying. it constitutes a deep-violet powder oll=lde in wate and alcohol with an in tead of those indicated in the examples, other acridin dyestull's can he transformed into silver compounds showing analogous properties. For the silver nitrate employed in the examples other convenient silver compounds can he'emploved. .\lso the other conditions may he varied within wide limits.

What we claim l 3 y l. The herein descrihtal. process for the namnfzu-ture of V'aluahle disinfectants, consisting in acting: on an acridin dyestufi' with a soluhle silver salt. in presence of a solvent.

2. The. herein described process 'for the imlnal'acturc of valuable disinfectants of the acrid n Stl'lt consisting in a ting on an acridin dsestull' alhylnled at the aeridin nitrogen with a soluble silver salt, in presence of a solvent. 3. As new products, the herein described disinfectants of the aeridin series, constitutin},' red to black powders, which dissolve in water with red to green colorations, in alcohol, acetic ether, glacial acetic acid and acetone with stron; fl'iorescences and in concentrated sulfuric acid with yellow to red eolorations, and acting still, when in so lutions of great dilution, strongly growth checking on hm teria and especially on streptococcus and -plenitis hacilli.

4. .\s a new article of manufacture the herein described silver compound of the 2 :7-

the acridin nitrogen. which constitutes a brown red powder dissolving in water with a red-orange coloration. in alcohol with an ol:lnge- \'ello\\ coloration and a strong lint rescence, in acetone. acetic ether and glacial acetic acid with \'ello\\'-;'reen lluoresceiu-es and in concentrated sulfuric acid, with a pure \'ellow coloration and which acts still, when in solutions of srreat dilution, .sll'ollfil) growth ('llt'tltlli; on hacteria and especiall 0n streptococcusancl splenitis hacilli.

in witness whereof we have hereunto signed our names this 27th day of Decemlwr, 1916, in the presence of two suhscrihing, witnesses.

l)u. no. IAlh HUSSY. Du. lniL. MAX llAR'lh'lANN.

\Vitnesses (.aln. ()j Sin-ulna, Ammxo Buanx. 

